Manager Technical Support

Sentry; Toronto; Hybrid; CAD 165,000; Full time

Job summary

A leading software monitoring company in Toronto seeks a Technical Support Manager to lead and mentor a team of Support Engineers. The ideal candidate will have over 8 years of experience in technical support or software engineering, and be adept in debugging code in languages like Python and JavaScript. Responsibilities include active participation in support requests and engaging with the developer community. A base salary of $165,000 CAD is expected, alongside additional benefits.

Benefits

Employee benefit plans

Incentive compensation

Equity grants

Paid time off

Group health insurance

Qualifications

• 8+ years of total experience in technical support, software engineering, or sales engineering.
• 2+ years of people management or team lead experience.
• Deep Technical Proficiency particularly in Python and JavaScript.

Responsibilities

• Lead a team of Support Engineers and resolve complex technical escalations.
• Serve as the ultimate escalation point for questions regarding Sentry's SDKs.
• Engage directly with users in public channels like Discord and GitHub.

Skills

Technical support

Software engineering

People management

Debugging code

Python

JavaScript

CI/CD

APIs

Tools

Zendesk

JIRA

Linear

Job description

About Sentry

Bad software is everywhere, and we’re tired of it. Sentry is on a mission to help developers write better software faster so we can get back to enjoying technology.

With more than $217 million in funding and 100,000+ organizations that believe we’re on to something, we're building performance and error monitoring tools that help companies like Disney, Microsoft, and Atlassian spend less time fixing bugs and more time building products.

Sentry embraces a hybrid work model, with Mondays, Tuesdays, and Thursdays set as in-office anchor days to encourage meaningful collaboration. If you like to selfishly build things that make your digital life better, come help us build the next generation of software monitoring tools.

About the Role

At Sentry, our customers are software developers. Solving their problems is complex, technical, and requires deep code literacy. We don't believe in "managers who don't know the product." We are looking for a Technical Support Manager who leads from the front lines.

You will lead a team of high-performing Support Engineers, but you won't be managing from an ivory tower. You will be a "Player-Coach" - spending a significant portion of your week in the queue, handling the most complex technical escalations, debugging code in open-source repos, chatting with engineers at Discord, and acting as the primary Subject Matter Expert (SME) for your team.

You are a former engineer or high-level support architect who loves the technical hunt but is ready to force-multiply that passion by mentoring a team. You will drive success not just by tracking metrics, but by showing your team how to solve the unsolvable.

In this role you will

Lead from the Front (Technical Execution):

• Be the Technical SME: Serve as the ultimate escalation point for complex questions regarding Sentry’s SDKs, trace propagation, and more.
• Active Queue Participation: Dedicate a portion of your week to answering inbound support requests, keeping your product knowledge sharp and setting the standard for quality.
• Triage & Debug: Triage, reproduce, and report complex product bugs. You will be expected to read source code to distinguish between a user error and a true platform bug before escalating to Engineering.
• Community Engagement: Engage directly with users in our public channels (Discord, GitHub) to solve problems and represent the Sentry brand technically.

Manage & Mentor (Team Leadership):

• Develop the Team: Conduct code reviews on ticket responses, provide deep technical feedback, and mentor engineers on debugging strategies and software fundamentals.
• Drive Performance: Own your team’s core metrics (CSAT, Response Time, Resolution Time) and workload balancing.
• Shape the Knowledge Base: Not only write articles yourself but curate the team's output to ensure our internal guides and customer-facing docs are technically accurate and up-to-date.
• Incident Command: Participate in the on-call rotation for high-severity issues and act as the Incident Commander for support during critical outages.

You’ll love this job if

• You are a "Tinkerer-in-Chief": You love leadership, but you miss the thrill of fixing a broken build or finding a needle-in-a-haystack bug.
• You lead by doing: You believe the best way to earn a team's respect is to be the person they turn to when they are technically stuck.
• You are obsessed with "The Why": You don't just want your team to close tickets; you want them to understand the underlying architecture of why the error happened.
• You thrive in the deep end: You are comfortable reading stack traces in languages you might not write fluently, and you can explain complex technical concepts to both junior devs and CTOs.

Qualifications

• 8+ years of total experience in technical support, software engineering, or sales engineering.
• 2+ years of people management or team lead experience, with a track record of hiring and mentoring technical talent.
• Deep Technical Proficiency: You must be able to read and debug code. Experience with Python, JavaScript, or other languages is required. You should be comfortable opening a browser console or a terminal to reproduce an issue.
• Modern Stack Knowledge: Strong understanding of the modern dev landscape (CI/CD, APIs, Microservices, Frontend vs. Backend, Observability).
• Hands-On Philosophy: A willingness to roll up your sleeves and work tickets. If you are looking to move away from technical work entirely, this is not the role for you.

Bonus Qualifications

• Previous experience working as a Software Engineer or in a DevOps role.
• Active contributions to Open Source projects (please share your GitHub!).
• Experience implementing Support tools or workflows (Zendesk, JIRA, Linear).

The base salary that Sentry reasonably expects to pay for this position is $165,000 CAD. A successful candidate’s actual base salary (or hourly wage) amount will be determined by a variety of relevant factors including, without limitation, the candidate’s work location, education, work and other relevant experience, skills, and job-related knowledge. A successful candidate will be eligible to participate in Sentry’s employee benefit plans/programs applicable to the candidate’s position (including incentive compensation, equity grants, paid time off, and group health insurance coverage). See Sentry Benefits for more details about the Company’s benefit plans/programs.

Equal Opportunity at Sentry

Sentry is committed to providing equal employment opportunities to its employees and candidates for employment regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, veteran status, or other legally-protected characteristic. This commitment includes the provision of reasonable accommodations to employees and candidates for employment with physical or mental disabilities who require such accommodations in order to (a) perform the essential functions of their jobs, or (b) seek employment with Sentry. We strive to build a diverse team, with an inclusive culture where every teammate can thrive. Sentry is an open-source company because we believe that everyone, everywhere, should have the ability and tools to make great software. Software should be accessible. That starts with making our industry accessible.

If you need assistance or an accommodation due to a disability, you may contact us at [e-mail].

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